Synthesis 2014; 46(03): 375-380
DOI: 10.1055/s-0033-1338564
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Chiral C 1-Symmetric N-Heterocyclic Carbene Ligands: Application toward Copper-Catalyzed Homocoupling of 2-Naphthols

Michael Holtz-Mulholland
Département de Chimie, Centre for Green Chemistry and Catalysis, Université de Montréal, CP 6128 Station Downtown, Montréal, QC, H3C 3J7, Canada   Fax: +1(514)3437586   eMail: shawn.collins@umontreal.ca
,
Shawn K. Collins*
Département de Chimie, Centre for Green Chemistry and Catalysis, Université de Montréal, CP 6128 Station Downtown, Montréal, QC, H3C 3J7, Canada   Fax: +1(514)3437586   eMail: shawn.collins@umontreal.ca
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Publikationsverlauf

Received: 13. August 2013

Accepted after revision: 30. Oktober 2013

Publikationsdatum:
26. November 2013 (online)


Abstract

Novel chiral C 1-symmetric NHC ligands can be prepared via dialkylation of chiral imidazoline scaffolds. Asymmetry in the ligand/metal complexes results from a chiral relay effect. The C 1-symmetric nature of the NHC ligand was proposed to allow for improved reactivity versus other achiral and chiral NHC complexes. The benefit of such ligands was demonstrated in copper-catalyzed oxidative coupling reactions.

Supporting Information

 
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